Cacodylic acid
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| Cacodylic acid | |
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| Other names | Dimethylarsenic Acid |
| Molecular formula | C2H7AsO2 |
| Molar mass | 137.9977 g/mol |
| CAS number | [] |
| Solubility (water) | Soluble, 66.7 g/mL |
| Melting point | 300 °C |
| Disclaimer and references | |
Cacodylic acid (also called dimethylarsinic acid) has the chemical formula (CH3)2AsO2H.
Derivates of cacodylic acid, cacodylates, were frequently used as herbicides. Sodium cacodylate is frequently used as a buffering agent during the preparation and fixation of biological samples for transmission electron microscopy.
Agent Blue, used as one of the defoliants in the Vietnam War, was a mixture of cacodylic acid and sodium cacodylate.
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[edit] History
Significant early research into cacodyls was done by R. W. Bunsen at the University of Marsburg. Bunsen said of the compounds, "the smell of this body produces instantaneous tingling of the hands and feet, and even giddiness and insensibility...It is remarkable that when one is exposed to the smell of these compounds the tongue becomes covered with a black coating, even when no further evil effects are noticeable". His work in this field led to an increased understanding of the methyl radical.
Cacodyloxide, ((CH3)2As)2O, was the first organometallic compound.
[edit] Synthesis
In the 1700s it was known that combining As2O3 and four equivalents of potassium acetate (CH3CO2K) gives a product called "Cadet's fuming liquid" which contains cacodyl oxide, ((CH3)2As)2O.
[edit] Health effects
Cacodylic acid is highly toxic by ingestion, inhalation, or skin contact. Once thought to be a byproduct of inorganic arsenic detoxification, it is now believed to have serious health consequences of its own. It has been shown to be teratogenic in rodents, most often causing cleft palate but also fetal fatality at high doses. It has been shown to be genotoxic in human cells, causing apoptosis and also decreased DNA production and shorter DNA strands. While not itself a strong carcinogen, cacodylic acid does promote tumors in the presence of carcinogens in organs such as the kidneys and liver.
[edit] See also
[edit] References
- Kenyon, E. M.; Hughes, M. F. "A Concise Review of the Toxicity and Carcinogenicity of Dimethylarsenic Acid." Toxicology 160 (2001): 227-236.
- Eschenbroich, C; Salzer, A. (1992) Organometallics, 2nd Edition
- Bunsen Biography
[edit] External links
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